On my 18 hour Spring Break road trip with the kids, we passed a few hilarious city names that really made an incredibly long adventure quite tolerable. One that made me think they had an identity crisis was Texarkana, Arkansas. Then when we passed Hope Arkansas, their tag line was home of Bill Clinton and Big Melons (I kid you not. Apparently they are known for extremely large watermelons).
Here are a few other Witty Cities: